


Drive

by LightLeadingMe



Category: Will & Grace
Genre: F/M, PWP, Plot What Plot/Porn Without Plot, Public Blow Jobs, Public Sex, Road Trip, Smut, backseat shenanigans
Language: English
Status: Completed
Published: 2018-05-21
Updated: 2018-07-04
Packaged: 2019-05-09 15:00:38
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 4
Words: 4,232
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14718312
Author URL: https://archiveofourown.org/users/LightLeadingMe/pseuds/LightLeadingMe
Summary: The gang goes on a road trip to Vermont. Karen gets bored in the backseat. [COMPLETE]





	1. Goodnight, Sleepy Head

_My hands wrapped around the stick shift_  
_Swerving on the 405,_  
_I can never keep my eyes_  
_Off this_

 _My neck, the feeling of your soft lips_  
_Illuminated in the light,_  
_Bouncing off the exit signs_  
_I missed_

Jack stared blankly out the window at the country road passing by them. Will and Grace decided to take a little road trip to Vermont for the weekend and Jack and Karen tagged along at the last second. They were staying at a cabin in the woods, similar to the one Karen owned. Due to Jack and Karen getting a late start, the gang didn't leave until 5 pm, perfect time for downtown traffic. By the time they finally got on the road, it was almost 6:30 which meant they wouldn't be arriving at their destination until almost midnight. Grace had fallen asleep almost as soon as the city lights dimmed into country which left Jack and Karen to entertain (annoy) Will for the rest of the drive. 

The sunset had fast set and the night came in, the only lights illuminating the road coming from the cars zooming down the country highway. Will, growing annoyed with Jack and Karen's antics behind him, turned up the radio to drown on the sounds of them giggling and teasing him from the backseat. It was nearly 10 pm now and Karen since then had rest her head against Jack's shoulder, her eyes closed and her breathing even. Jack felt his eyes grow heavy as well, but kept himself awake in case Will needed someone to talk to. He glanced down at Karen on his shoulder and smiled. She always looked so serene and peaceful in her slumber. Just as he turned his gaze back out the window, he felt Karen shift into him, her body turned towards his so her chest was against his arm and her nose brushing his neck. Her hand slid up his thigh and rest on his crotch causing Jack to bite his lip. Her hand slowly began to move up and down gently, her nails tracing his dick through his pants. He tried to ignore it, knowing she was asleep and probably dreaming, but his body couldn't help but react to the attention it was getting. 

 She stroked him harder, his dick stiffening under the material of his khakis and ministrations she was performing on it. He opened his mouth to wake her up, but felt her lips brush against his ear, her breath hot. "Do you want me to stop?" she asked seductively. Her tongue traced his ear and dipped in once before her teeth latched on to his ear lobe.

Jack shuddered and glanced up at the back of Will's head. He was singing loudly to a Queen song and using the steering wheel as his drum set while Grace snored loudly in the passenger seat next to him. Jack slowly shook his head and even though he couldn't see her face, he knew Karen was smiling at his answer. He looked down at his lap and watched as she unzipped his pants and sneaked her hand inside. In a few seconds she had his dick out, completely hard and begging for touch, and her hand began to pump him slowly. Jack bit his lip hard to keep from moaning. He knew Will wouldn't be able to hear him through the loud music and his screeching along to the song, but he didn't want to raise any suspicions. 

Karen nipped at his neck before shifting again, bringing her head down to his crotch. Jack knew if Will looked back it would only seem like Karen was resting her head in his lap as she slept. He threw his head back and closed his eyes, swallowing hard as he felt Karen envelope him in her mouth. He slouched slightly in his seat, spreading his legs out further and placing his hand on the back of Karen's head. He was grateful she didn't have her hair piece in today otherwise he wouldn't be able to grab a fistful of her dark locks. He couldn't hear it, but he felt the vibrations of her moaning against his cock and he gazed down at her. Her face was covered by her hair so he used his other hand to brush it away, watching as she took all of him in her mouth, the tip of his cock tapping the back of her throat as she bobbed up and down. He felt his orgasm rapidly approaching and he let out a sigh, his muscles tightening. 

Karen raised her head and wrapped her lips tight around the head of his cock, her tongue swirling and licking the underside as her hand pumped him up and down rhythmically. Jack squeezed his eyes shut and his head smacked against the back of the seat as he came hard, his cock spurting into Karen's mouth. She took it all and then released him slowly. Jack brought his eyes back to her as he calmed down and Karen stuck her tongue out at him, showing him some of his cum before she swallowed, licking her lips and winking at him. She tucked him back into his pants and zipped him up, placing a few pats on his crotch before she kissed his cheek and turned away from him, muttering a 'goodnight' his way.

Jack sat in astonishment at what just transpired and didn't know what to do with himself. He looked next to him and saw Karen reach into her purse for a flask, taking a few swigs and then tossing the flask into the back of the SUV.

"Karen!" Will admonished from the front. "I told you to stop throwing things back there!"

"Well where else am I supposed to throw my trash, _mom_?!"

Jack watched the argument as it continued for a while, eventually waking Grace up. He swallowed loud, not sure if what just happened actually happened or if he dozed off and dreamt the whole thing. What he did know for sure was that as his friends continued to argue with each other during the last hour of their drive to Vermont, Jack had a very uncomfortable hard-on. 


	2. Good Morning, Sleepy Head

**Summary for the Chapter:**

> Jack decides to wake Karen up in a fun way.

Not too long after arriving at the cabin, the four friends crashed in their rooms. Since Will and Grace had booked the cabin a week ago without knowing Jack and Karen would be joining them, it was only a two bedroom so they had to pair off. The original plan was for Grace and Karen to share one room while Jack and Will bunked across from them, but then Jack swore he caught Will checking out his ass as they unloaded the car and threw the biggest hissy fit one could throw in the middle of the woods at one am until Grace and Will relented and let Jack and Karen share a room. 

They didn't bother unpacking anything, almost too exhausted to change for bed. Jack simply stripped down to his t-shirt and boxers while Karen grabbed his discarded sweater and threw it over her head, her undies the only thing underneath. They climbed into the bed and passed out the second their heads hit the pillows. 

Jack woke first in the morning to the sound of Will banging on his door. He untangled himself from Karen and opened the door to find a fully dressed Will behind it. "What do you want? Karen's still sleeping," he asked tiredly.

Will rolled his eyes, his hands on his hips. "Well, wake Vampira and get downstairs. We made breakfast."

Jack glanced back at Karen's still sleeping form on the bed and then at the clock on the wall. "Look," he addressed Will. "Go ahead and eat, we'll be down later."

"Are you sure?" Will asked. "After we're done eating, Grace and I were going into town to do some shopping."

"Shopping?" Jack grimaced. "In this podunk town? What the hell you gonna buy? An antique toaster?"

Will frowned in confusion. "Why a toast-"

"I'm tired, leave us alone." He closed the door in Will's face and turned back to the bed. Karen had shifted since he got up and was now on her back with one arm above her head while the other rest across her stomach. The sheets were kicked down by her feet and one leg was spread out to the side in his spot, the other going the opposite direction. She was taking up the entire bed. The sweater she wore, _his sweater_ , had ridden up to her stomach, exposing her black panties, a stark contrast to her alabaster skin. 

Jack shook his head and smiled. He was about to turn to go to the bathroom when he heard Karen moan in her sleep. He watched carefully as she raised her hips slightly and bit her lip, a look of frustration mixed with pleasure crossing her features. Jack's jaw dropped at the realization that she was having a sex dream. Flashes of the night before sprung to his mind and smirked deviously, knowing the perfect way to wake her up.

He climbed onto the bed from the end and slid onto his stomach between her legs. He placed feather light kisses upon the skin on the inside of her thighs, making his way up until he reached the edge of her panties. He placed a kiss against her, feeling the already damp material touch his lips. He heard her sigh above him and glanced up quickly, relaxing when he concluded that she was still asleep, her breaths still deep. He used his fingers to slowly move the gusset of her panties aside, exposing her clean shaven pink lips to him. Tentatively, Jack placed another tender kiss against her and Karen gasped in her sleep. He stuck his tongue out and traced her lips until he found the slightly hardened nub near the top. He wrapped his lips around it and flicked his tongue back and forth, feeling more moisture escape her on his chin. Karen was moaning freely now and he looked up just in time to see her pop her eyes open in surprise, raising herself up to her elbows.

"What the-" She noticed just what was going on between her legs and felt his tongue enter her. At the same time, Jack moved his hand and pinched her clit between his fingers, rubbing in circles. Karen's eyes rolled back and she fell back against the pillows as her orgasm washed over her. "Ohhh fffffuck!"

Jack licked at her juices, cleaning her up, and then moved her panties back into place. He patted her thigh and then stood from the bed, throwing a 'good morning' over his shoulder as he walked to the bathroom, closing the door behind him. 

 

 


	3. Chapter 3

It was Sunday morning, the last day the group of friends would be in Vermont. They spent all day Saturday shopping at antique malls and checking out the gorgeous views the state had to offer. Today they were to pack their things, go out to brunch, and then get back on the road to be home in time for dinner before going their separate ways since they all had work in the morning. 

It was early, the sun barely rising over the horizon when Karen woke. She was once again wearing one of Jack's sweaters and a pair of undies to bed. The sleeves fell past her hands and the soft knit was warm and cozy. Lying next to her, Jack stirred in his sleep, a small pout on his lips. She looked over at him, a grin covering her face when she saw the bulge in his boxer briefs. They hadn't spoken of their recent acts of sexual activity, but Karen had a feeling that they didn't need to. She sat up and ran a hand through her long, dark hair before crawling on top of Jack. His eyes fluttered open just as she straddled his thighs, her hand smoothing along his hard cock over his underwear.

"Kare..." he whispered, watching her through hooded eyes. 

She smiled at him and scooted herself up further so she was hovering over his hips. She lowered down slowly, gasping when she felt him between her legs. She leaned forward and placed her hands on his bare chest while his ran up her thighs, settling on her ass, and Karen began to grind down on him. They moaned together, their eyes fluttering as a soft pleasure coursed through them. Jack squeezed her cheeks in his hand, guiding her as she rotated her hips, feeling her heated core on his stiff erection. He looked down and saw the head of his cock poking from the waistband of his briefs. Karen seemed to notice as well and smirked at him as she raised herself to push his underwear down just enough to set him free, the cool air hitting his hot body and making him shiver. She resumed her humping on his lap and Jack groaned loudly, the sensation of her soaked panties rubbing him made his body feel aflame. 

Karen bit her lip and grabbed Jack's wrists, bringing his hands up under her shirt and placing them on her breasts. He immediately began massaging her tits and Karen moaned appreciatively, her eyes dark with lust. Jack looked down where their bodies were pressed together, the sight so erotic it took everything in him to not cum prematurely. He removed one hand from her chest and hooked it in her panties, pulling the material to the side so Karen's bare pussy was now in full contact with his dick. 

"Jack," Karen gasped, looking down into his eyes. 

He smiled and pinched her nipple, loving her sounds of pleasure as they worked for their releases. He could feel her clit brushing with the head of his cock in every pass she made and it caused him to tense up, his orgasm approaching quickly. 

"Oh shit," she cursed and began rubbing harder, her orgasm starting to spread throughout her body. Karen dug her nails in Jack's chest and then cried out, her juices pouring out of her and on to Jack.

He grunted as he came all over his abs and let go of Karen's underwear, bringing his other hand down from under her sweater. Karen sighed, her thighs trembling slightly from the aftermath of her release. She glanced down, seeing his cum all over his stomach and hers on his dick. She grinned slyly and lowered her head down, her tongue out as she began to lap around his abs and then she took his dick in her mouth, cleaning him up. He bit his lip, a whimper escaping him. Karen released him from her mouth and sat up before she leaned over, placing a hand on his chin, the other on the pillow by his head to steady herself. She opened her mouth, shoving her tongue between his lips and Jack accepted her in, growling as he tasted the mixture of himself and Karen on her tongue. They parted for air a few moments later and she lifted herself off his lap, adjusting her undies back into place.

Karen fell back next to him, bouncing a little on top of the plush mattress. Jack looked over, licking his lips and opened his mouth to speak when a knock on the door startled them both. Jack quickly pulled his briefs back up just in time for Will and Grace to burst through the door. Karen let out a giggle at the shocked looks on their faces.

"You guys!" Grace exclaimed. "Why aren't you up? We need to be on the road by one!"

Will frowned at the flushed faces of his two friends, his hands on his hips in question. "Are you guys okay?"

Jack put on a fake pout and looked back at Karen who could barely contain her laughter. He shrugged at Will. "Uhh, yeah? Just tired."

Will raised an eyebrow, looking like he wanted to pursue his questioning, but Grace interrupted him. "Let's go you two! Those pancakes are not going to eat themselves!"

Jack sprung from the bed and began to gather his clothes. "Okay, mom and dad! Just let us get ready!"

Karen stood from the bed and brushed past Jack on her way to the bathroom, giving him a flirty wink. 

"Just hurry up," Grace pleaded. "I'm starved!"

"You just ate a bagel," Will tossed at her.

"Well you woke me up so early! I needed something to tie me over!"

"So you had breakfast."

"No, I had a pre-breakfast. Who the hell just eats a bagel for breakfast?"

Jack rolled his eyes and pushed his two friends out of the room as they continued their arguing and closed the door behind him. He let out a breath of relief and locked his eyes on the bathroom door where Karen disappeared behind.

 


	4. Chapter 4

The car ride back home was quiet. Will and Grace quickly grew tired of their game of "I Spy" so they turned on the radio instead and began to sing obnoxiously along. Once again sitting in the back of the car, Jack and Karen rolled their eyes and tried their best to ignore the awful singing of their friends. Around the second hour of the drive, Jack grew increasingly more bored than before and glanced to his left to see Karen staring blankly out the window. A thought percolated in his mind for a few moments before he grinned slyly and scoot himself over to her. He lay his head on her shoulder and rest his arm over her stomach, most of his body covering her. 

Karen smiled at him and pat his head, thinking he was cuddling up to her to sleep, and turned her attention back to the passing cars and scenery. Jack's fingers toyed with the edge of her blouse before slipping beneath the material, brushing the softness of her skin on her stomach. Karen still paid no mind and he smirked. He buried his nose in her neck and let his body relax, making her think he was about to settle down for his nap, and then pushed his hand all the way up her shirt, his fingers pinching her nipple. 

They both gasped; Karen surprised at Jack's stimulating touch and Jack at the discovery of her not wearing a bra. He pressed his lips to her neck and swirled his tongue teasingly, feeling her pulse quicken against his mouth. He removed his hand from under her shirt and slid it down to her dress pants, unbuttoning them and pulling the zipper down tantalizingly slow. He pushed his hand beneath her underwear and used his two middle fingers to find her already swollen clit. Jack didn't know if it was from their little dry hump session this morning or from his ministrations currently, but he didn't really care. He heard Karen whimper quite loudly and he raised his head to bite her earlobe.

"Sshhh," he whispered, pressing his fingers harder against her. "We don't want to get caught."

Karen nodded her head vigorously, her teeth biting her bottom lip. Jack brought his lips back down to her neck and he continued to tease her between her legs. He felt her slouch slightly in her seat, her legs parting just enough for him to have more room and he gladly shoved two fingers into her roughly. He felt her body tense against him and a grunt of pleasure escape her lips.

"You okay back there?" Will asked from the front.

Karen knit her eyebrows together, locking eyes with the lawyer in the rearview mirror. "Y-yeah, honey."

"Is Jack sleeping already?" he scoffed, a small smile gracing his lips.

Karen nodded, unable to vocalize her response as Jack pinched her clit with his thumb and curled his fingers up to stroke the rough inner wall inside of her. 

Will's eyes went back to the road with a shake of his head. "Well, we've about two more hours before we get back into the city. Grace, could you hand me the Twizz- Grace!"

"What?!"

"How did you already eat an entire bag of Twizzlers?!"

Karen tuned out the argument in the front seat and concentrated on Jack's hand between her legs. She closed her eyes and pressed her head back against the headrest, licking her lips and letting the pleasure begin to consume her. Just as she felt herself near the edge, Jack slowed down the thrust of his hand, slipping his fingers out of her completely. She frowned, but then let out a satisfying breath when he started to rub her clit again. He latched his teeth to her collarbone and gave her a hickey as he pushed his fingers back into her. Karen felt tears rush to her eyes when she began to crash over the edge and then the feeling was lost again and she let out a shuddering sigh of frustration.

Jack chuckled into her neck, his fingers once again teasing her clit. He knew she wouldn't yell at him with their friends less than two feet away from them so he felt very comfortable with teasing her relentlessly. He continued this for the duration of an hour, Karen edging the entire time, but never allowed to cum. At one point, Jack removed his hand completely and he heard Karen sob sharply, drawing the attention of Will once again.

"Kare, are you sure you're okay?"

"I'm fine, Wilma!" she shrieked at him, her frustration making her snap. 

Will shrugged and went back to his driving while Karen grumbled under her breath. Jack brought his fingers, wet with her arousal, to his lips and licked them clean before he reached for the buttons on her button down. He shifted in his position so it looked like he was laying his head on her chest as he slept, but in reality he reached into her blouse and pulled her tit out. Karen wrapped her arm around his back and gripped his hair as he lifted her boob to his mouth, his tongue flicking against the hardened peak of her nipple. 

 He felt her shiver and he closed his mouth around the nub, suckling gently at her. Karen sighed happily and let him continue his torture on her, feeling the tension in her body rise up again. Jack laid hickeys all along her breast, knowing that any low cut shirt or dress she wore the next few days would easily show the lovebites. The thought exhilarated him and he moaned as he bit down on her gently. Karen gasped again and gripped his hair, guiding his mouth back to her nipple where he greedily engulfed her bosom. He slipped his hand back into her panties and inserted his fingers into her again. As he moved his hand he realized she was so wet that each thrust made a squelching sound. Not wanting to get caught, Jack removed his fingers and placed them on her clit. He rubbed quick, rough circles against her and Karen quietly squeaked. Her nails dug into his scalp and her entire body stiffened as she finally came, a whisper of his name escaping her lips. 

Jack cupped her, gathering her cum on his fingers and then pulled his hand out of her pants. He released her nipple from his mouth and looked up at her as he lifted his hand to his lips. Before he could lick his fingers, Karen grabbed his wrist in her free hand and wrapped her lips around two of his digits, divesting his fingers of her own juices. Jack watched, his jaw slightly slack and his heart racing. Karen stared him down as her tongue swirled around his fingers, sucking them and then letting them go with a small 'pop'. 

"Aaaand we're home!" Will announced from the front seat as he pulled into a parking spot.

Karen discreetly buttoned her shirt and pants as Jack lifted himself from her, stretching as if he just woke up. "Wow," he fake-yawned. "What a relaxing ride. Wouldn't you say so, Kare?"

Karen glared in his direction and didn't respond. Jack just grinned boyishly at her and opened the door to get out and stretch his legs. Karen followed and soon they found themselves exiting the elevators on to the 9th floor.

"Karen, do you want me to call you a cab?" Will asked as he unlocked his apartment door.

"No, honey," Karen waved him off and followed Jack to 9A. "I'm gonna spend the night with Jackie. It's too late to go home now."

Will frowned. "It's 7:30."

Karen nodded and licked her lips. "Yeah, but I owe Jackie a favor." She kept her eyes on Will and Grace's confused faces as she carefully slipped her hand between Jack's legs from behind, her hands cupping his balls through his slacks. "And it's payback time."

Jack held back a groan, his fingers fumbling with the keys as he tried to put them in the lock of his door. 

"What favor do you owe Jack?" Grace asked curiously.

Karen grinned when Jack finally opened the apartment door and practically ran inside, tripping over his luggage as he did. She winked at Will and Grace and shrugged as she followed him inside. "Goodnight, guys."

Will and Grace stared in bafflement as the door to 9A shut. 


End file.
